Diastereoselective Synthesis of Dihydropyrans via Prins Cyclization of Enol Ethers: Total Asymmetric Synthesis of (+)-Civet Cat Compound

2013 ◽  
Vol 78 (23) ◽  
pp. 12182-12188 ◽  
Author(s):  
Sabera Sultana ◽  
Kiran Indukuri ◽  
Manash J. Deka ◽  
Anil K. Saikia
Keyword(s):  
Asymmetric Synthesis ◽  
Diastereoselective Synthesis ◽  
Prins Cyclization ◽  
Enol Ethers

Diastereoselective Synthesis of Substituted Tetrahydrofurans via Prins Cyclization of Enol Ethers

2014 ◽  
Vol 79 (18) ◽  
pp. 8592-8598 ◽  
Author(s):  
Paramartha Gogoi ◽  
Vijay K. Das ◽  
Anil K. Saikia
Keyword(s):  
Diastereoselective Synthesis ◽  
Prins Cyclization ◽  
Enol Ethers

Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D

2014 ◽  
Vol 12 (36) ◽  
pp. 7026-7035 ◽  
Author(s):  
Anil K. Saikia ◽  
Kiran Indukuri ◽  
Jagadish Das
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Cyclization Reaction ◽  
Diastereoselective Synthesis ◽  
Prins Reaction ◽  
Prins Cyclization ◽  
Acyliminium Ions

A diastereoselective synthesis of 4-O-tosyl piperidine containing azabicyclic derivatives has been established via Prins cyclization reaction. This protocol has been applied for the total synthesis of (±)-epi-indolizidine 167B and 209D.

Diastereoselective Synthesis of (3R,5R)-γ-Hydroxypiperazic Acid

Synlett ◽  
2021 ◽  
Author(s):  
Juan R. Del Valle ◽  
Taylor A. Gerrein ◽  
Yassin M. Elbatrawi
Keyword(s):  
Asymmetric Synthesis ◽  
Late Stage ◽  
Ring Formation ◽  
Peptide Chain ◽  
Nonribosomal Peptides ◽  
Diastereoselective Synthesis ◽  
Hydroxylation Reaction ◽  
Enolate Hydroxylation

AbstractWe report an asymmetric synthesis of the (3R,5R)-γ-hydroxypiperazic acid (γ-OHPiz) residue encountered in several bioactive nonribosomal peptides. Our strategy relies on a diastereoselective enolate hydroxylation reaction and electrophilic N-amination to provide the acyclic γ-OHPiz precursor. This orthogonally protected α-hydrazino acid intermediate is amenable to late-stage diazinane ring formation following incorporation into a peptide chain. We determined the N-terminal amide rotamer propensity of the γ-OHPiz residue and showed that the γ-OH substituent enhances trans-amide bias relative to piperazic acid.

Diastereoselective synthesis of pitavastatin calcium via bismuth-catalyzed two-component hemiacetal/oxa-Michael addition reaction

2015 ◽  
Vol 13 (38) ◽  
pp. 9813-9819 ◽  
Author(s):  
Fangjun Xiong ◽  
Haifeng Wang ◽  
Lingjie Yan ◽  
Lingjun Xu ◽  
Yuan Tao ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Addition Reaction ◽  
Diastereoselective Synthesis ◽  
Michael Addition Reaction ◽  
Two Component ◽  
Pitavastatin Calcium

An efficient and concise asymmetric synthesis of pitavastatin calcium (1) starting from commercially available (S)-epichlorohydrin is described.

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